


PART ONE: Simon - The Walking Dead 250 word One-shots

by SimonsSavior



Series: Simon - The Walking Dead - One Shots [1]
Category: The Walking Dead (TV)
Genre: Caring Simon, F/M, Fluff, Fucking, Protective Simon, Reader-Insert, Simon being cute, Smut
Language: English
Status: Completed
Published: 2018-01-28
Updated: 2018-02-19
Packaged: 2019-03-10 15:53:26
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 13
Words: 3,250
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13504797
Author URL: https://archiveofourown.org/users/SimonsSavior/pseuds/SimonsSavior
Summary: Collection of one-shots featuring Simon/Reader, inspired by prompts that were given to me and a maximum of 250 words per fic. Each prompt is the chapter title.





	1. I Can't Believe You

“I can’t believe you.” You roll your eyes at Simon as you climb begrudgingly into his Jeep beside him.

“What?” He frowns.

“You know what.” You huff.

“Enlighten me.” He smirks, pulling the door shut and shifting in his seat.

“You, jumping at the chance to get me in your truck even though you know I always ride with Laura. Negan always pairs me with Laura. You’re just so…” Your words trail as you think of what to say to him.

“Charming? Handsome?” He starts the engine and grins widely and you try to hide the smile creeping onto your lips.

“Obvious. You’re so fucking obvious.” You fold your arms.

Simon frowns genuinely this time as he stares out at the road. “I’m what?”

“I thought we were keeping -” You wave your hands back and forth between the two of you. “ _\- this_ , quiet. I mean, Laura is already asking questions about us.”

“What sort of questions?” He raises an eyebrow.

“The ‘ _are you fucking?_ ’ kind.”

Simon runs his tongue along his teeth and reaches out to place a hand on your thigh. “But we _are_ fucking.”

“Yes but the whole Sanctuary doesn’t need to know.” You protest.

Simon slides his hand further along the inside of your thigh and squeezes gently. “They probably already know.”

“What? How exactly-” But Simon cuts you off.

“Oh, dove, the way you were screaming my name last night, hell. The Kingdom, The Hilltop and the entire Piss Patrol probably know, too.”

“Fuck off, Simon.”


	2. Not You Again

“Not you again…” You stare at Simon as he stands on the other side of the door with a bottle of tequila in one hand, two glasses in the other and a ridiculous smile on his face.

“Well, shit, that kinda hurts my feelings.” His smile drops and he pouts like a sad puppy. But you’re unable to keep a straight face as he stares with wide eyes, and you soon find yourself giggling at his absurd expression.

“Get in here.” You insist.

Simon sighs and rolls his eyes sarcastically. “Nah, if you’d rather I didn’t intrude on your evening I can always-”

“Shut up, Simon.” You protest with a grin, wrapping your hands around his neck and pulling him toward you. And he makes no attempt to resist your advances as you place your lips on his, instead wrapping his heavy arms around your shoulders, whilst keeping a careful hold on the bottle and glasses all at the same time.

Reluctantly, he breaks the kiss, pulling away and moving around you to kick the door shut. He places the glasses on the table and unscrews the cap from the bottle and you can’t help staring at his broad shoulders as he pours the drinks with his back turned to you.

But before he can offer you the drink, you press yourself into him, wrapping your arms around his middle and holding him tightly.

“I miss you when you’re not here.” You admit.

He breathes deeply. “I miss you, too.”


	3. Are You Upset With Me?

“Are you upset with me?” Simon questions, leaning forward from his place on the bed and resting his heavy arms on his knees.

You glance up from the table to study his face and he’s gazing at you with concern. “What? No. Why would you think that?” You shake your head and attempt a smile.

He raises an eyebrow. “You’re sitting over there looking miserable and you’ve barely said a word all evening.” He’s not wrong, and when you don’t reply he shifts himself to the edge of the bed and sighs, running a hand over his thick mustache. “I can go if you want.”

“No, don’t.” You insist, pushing yourself up from the table and dropping onto the bed next to Simon. “Sorry, it’s not you.”

Simon sighs heavily and turns, wrapping his arms around you and pulling you against his solid, warm chest. “I’m here if you wanna talk, dove. You know that?”

“I know.” You smile.

“So, you wanna talk?” You look up to find Simon staring at you.

“Not really.” You shrug.

“Uh-huh… Negan?”

“He’s an asshole.” You mutter, burying your face back into his chest. Simon chuckles. “Don’t tell him I said that.”

“He is.” Simon agrees. “And I won’t.” He kisses your forehead. “Let me talk to him. I’ll convince him to have you accompany me on runs. You can come help out at the Hilltop.” The thought of Simon having you stay by his side leaves you with a smile on your face.


	4. Stop Being So Cute

“Stop being so cute.” You glance at Simon as you lay side by side in the back of the pickup.

“Cute?” He chuckles. “I’ve been called a lot of things in my time but cute isn’t one of them.” He smiles and you can’t help smiling back as his finger repeatedly traces the words ‘I love you’ across the palm of your hand.

You shift against the truck bed and roll onto your side to better face Simon. He does the same, smiling warmly and you find comfort and safety in his eyes as he gazes at you; the brilliant white of the moonlight reflected in the pools of deep brown.

“Well,” You grin, “I think you’re cute.”

He raises an eyebrow. “That so?”

“Yup.” You tease.

Simon chuckles again before shifting his weight to guide you once more onto your back, entwining his fingers with yours and pinning both of your hands above your head. And then he presses his lips against yours; his kisses soft and gentle and barely there.

You close your eyes; feeling as though you might melt beneath him as his kiss deepens and his tongue dips briefly in search of yours. But to your disappointment he pulls away, grinning. “Cute’s just not gonna work for me, dove.” And with that he kisses you harder; his teeth grazing your lower lip and his grasp still tight on your wrists.

_Sure, you like it when Simon is cute, but you like it more when he’s not._


	5. I Can't Stand The Thought Of Losing You

“I can’t stand the thought of losing you...” Simon mutters, knelt down and dabbing gently with a cloth at your fresh cuts and grazes.

You roll you eyes. “Simon, it’s fine. It was just glass.”

He nods sarcastically. “You fell through a _window_.”

“But I didn’t get bit.”

Simon stops and stares at you with wide eyes and an unimpressed expression. “You _almost_ got bit.” He raises an eyebrow before resuming tending to your injuries.

You sigh, dragging yourself up from the tarmac and feeling like Simon is overreacting. But you know it’s only because he cares. “Look at me.” You lift your hand to his face; stubble coarse beneath your fingertips as you stroke his cheek. “I’m not going anywhere.”

Simon stands, balling up the cloth in his fist. “No shit. I’m not letting you disappear by yourself again. Ever.” He asserts. You drop your hand from his face and frown; it’s not Simon’s decision what you can and cannot do.

“That’s not up to you.”

“I think you’ll find it’s entirely up to me.” He disputes. “Since I’m the one in fucking charge around here.” You huff and he grins, seemingly pleased with himself because he knows he’s right.

“I did my job.” You protest.

“You nearly got yourself killed!”

Irritated by his arrogance, you turn to walk away; but he grabs your wrist and pulls you back, effortlessly.

“Just accept that I love you. And I’m gonna keep you safe, even if you hate me for it.”


	6. They're Going To Love You. Don't Worry!

**Notes for the Chapter:**

> This chapter is AU. The zombie apocalypse never happened!

“They’re going to love you. Don’t worry!” You attempt to reassure Simon, watching from the bedroom doorway as he rummages through his wardrobe and picks indecisively through different shirts.

“Who says I’m worried?” He mutters with his back turned to you. You roll your eyes and Simon shrugs his broad, heavy shoulders as he pulls out a dark blue shirt. He holds it up against himself, glancing in the mirror before turning to you. “This one?”

You respond with something between a nod and a shrug. “It’s just dinner.”

He stares at you. “It’s not _just_ dinner; it’s dinner with _your family_. First impressions are important.” He throws the shirt on the bed and saunters toward you with a smirk. “Remember the first time we met?”

You huff out a laugh as he wraps his hands around your hips. “I was drunk. You were drunk.” Your fingers trail through the dark hair on his chest. “What kind of first impression was that?”

“Yup.” He leans forward and places delicate kisses over your neck. “And we had _incredible, sex,_ for two people who’d just met.” He pulls your hips hard against his. “That’s a great first impression.” He grins.

“Okay,” you push him reluctantly away from you. “Just so we’re clear, Simon, when they ask how we met, you do _not_ tell that story.”

“The one where we did this?” He pushes you against the doorframe.

“Or this?” He kisses you fiercely.

“Or _this?_ ” He mumbles, fingers slipping below your waistline…


	7. This Was Fun. Let's Do It Again Some Time!

“This was fun. Let’s do it again some time!” Simon declares, turning back to Gregory with a vicious grin.

“You – You shot him. Why would you do that?” Gregory demands as he glances between Simon and you. You frown at him as a furious confusion settles on his face.

Simon replaces his pistol into its holster and sighs. “Gregory. Your man here-” He pauses, gesturing with one hand to the lifeless body on the floor as he waits to hear the man’s name. “Forget it, name’s not important.” Simon shakes his head when Gregory fails to answer him. “He, was carrying, _a gun_. Which as I’m sure you know, is against Negan’s _rules_.” He lowers his head. “Only _Saviors_ need guns.”

You find yourself staring at Simon and he shoots you a brief glance; his actions never fail to both terrify and excite you all at once, and he knows it.

“Well I – I imagine that, he… He had the gun for self-defense?” Gregory stammers.

“You didn’t know about this?” Simon questions.

“No. No of course not, I had no idea-”

“Then, Gregory,” Simon interrupts. “I think you should be thanking me!” Simon throws out his arms and grins his perfect grin, waiting expectantly for a thank you. “See, he was not being a team player, here. He could have wound up causing _you_ , a lot of trouble.”

Gregory nods. “Yes. Uh, thank you, Simon.” Simon chuckles and slaps him patronizingly on the shoulder before turning to you.

“Let’s go.”


	8. We Can't Go In There

“We can’t go in there.” You giggle as Simon pushes you up against the door.

“Says who?” He contests.

“Negan. He’ll _kill you_.”

Simon pauses, smiling deviously. “Negan’s not here.” He raises an eyebrow and clicks open the door, causing you to tumble backwards. He catches you, pulling you back to him and kicking the door closed.

For a moment you glance around the room; _Negan’s room_. But you don’t have time to take in how exquisite it all is before Simon has you pinned against the luxurious satin bedspread, his hands hastily working loose your belt.

You assist Simon in dragging down your jeans before he unfastens his own belt; freeing his impressive erection. And Simon is wasting no time; because although his facade may suggest he has no fear of being caught by Negan, you know he’s apprehensive of being here too long.

He grins as he wavers above you, teasing your wetness with his tip and causing you to inhale deeply, before eventually easing his way inside and filling you entirely.

“Fuck, _Simon_.” You moan his name as his hips rock against yours and he drives himself harder inside with each thrust. He moves to trace rough circles over you with his thumb, bringing you rapidly toward the edge of release.

It takes just minutes for Simon to bring you to orgasm; your body shuddering as you gasp with pleasure beneath him. And Simon is quick to follow, groaning as he spills himself deep inside of you.

**Notes for the Chapter:**

> Okay you have no idea how difficult it is to write smut in 250 words... Jeez. Hope I did okay.


	9. Wanna Go See A Movie With Me?

“Wanna go see a movie with me?”

“What?” You turn as Simon drops down onto the concrete steps beside you.

“You know,” he stares at you with a ridiculous expression on his face. “Like a date night.” He grins eagerly.

You laugh, shaking your head at him. “Date night? Is that what we’re doing now?”

He leans over and nudges your shoulder with his. “Come on. It’ll be fun.”

You smile as you consider his offer. You know he’d picked up an impressive new television on one of his most recent supply runs and, admittedly, spending the night cuddled up with Simon, watching a rom-com and pretending like the world hasn’t ended doesn’t sound like a bad idea.

“Will there be popcorn?”

“Um,” He thinks for a moment. “There’ll be ice cream.”

\---

When he opens the door to his room, Simon is holding two big bowls of ice cream, and without saying a word you take a bowl and reach up to press a firm kiss against his lips.

“Hello to you, too.” He raises an eyebrow before closing the door.

“So, what are we watching?” You plonk yourself down onto Simon’s comfortable two-seater sofa. He settles himself next to you and reaches for the remote.

“Con Air.”

You stare at him but he doesn’t pay attention. “ _Really?_ ”

“Yup.” When you don’t respond he turns to you. “Look we’re limited on DVD choices.” He shrugs.

“Bullshit…” You mutter, shaking your head with a smile and making yourself comfortable against him.


	10. You Have No Idea What You Do To Me

“You have no idea what you do to me.” Simon growls as he wraps his hands around your waist and pins you against his pickup truck. You attempt to hide a smirk as his tongue traces his lips; his gaze settling on your own lips. His eyes are heavy and he stares at you with a desperate hunger and you know he’d have you right there and then if he could.

Your hands trail quite deliberately over his impressively athletic frame; exploring every defined muscle before you tuck your fingers into his belt. He presses closer, eliminating the already scarce gap between you.

“I think I have some idea…” You grin, feeling his strained erection as he leans into you and runs his fingers through your hair. He traces your jaw and lips and chin; his hand eventually finding its way to rest against your throat whilst his other hand caresses your ass.

Then he lowers his mouth to yours; his lips gentle and mustache soft against your skin; contrasting with the couple days’ worth of rough stubble developed on his chin. His kiss deepens, tongue seeking permission to taste yours; and soon it becomes impossible to breathe as you’re lost in him.

“ _Hey, lovebirds_ , we got _shit to do_. You can get back to _fucking_ one another later.” Negan’s amused chuckle is enough to pull you both back into reality.

Simon’s kiss lingers for a moment longer before he eventually drags himself away with a sigh. “Sure thing, Negan.”


	11. As You Wish

“As you wish.” Simon nods with a malicious grin and pulls out his pistol, following Negan’s orders and taking aim at the man cowering before him.

“No, please – please don’t-” The man begs at Simon’s feet as Negan turns and walks away from the scene and you’re left standing between Simon and Dwight; rifle aimed at the rest of your captives.

This part of the job is always the hardest; Negan ordering the deaths of innocent men or women simply to prove a point to other survivors is something you still find hard to stomach. You know Dwight finds it hard, too. But not Simon; Simon revels in the authority handed to him by Negan and the power he wields over his victims.

“Shut, _up!_ ” Simon drawls. “No use in complaining. You all need to be taught a lesson and the lesson is; _not to fuck_ , with The _Saviors_.” And with that he pulls the trigger, smiling contentedly as the man’s lifeless corpse hits the ground.

\---

“How do you it?” You question, lying in the darkness beside Simon.

“Huh?” He mumbles, rolling toward you.

“How can you be so ruthless? So – _Negan?_ ”

“And yet so fucking charming all at once, right?” He presses a delicate kiss to your shoulder. “We have to do what we have to do, to keep this place safe; to keep the _people_ safe.” He sighs contentedly. “Just doing my job.” He pauses, moving closer. “It don’t change the person I am when I’m with you.”


	12. On Your Knees

“On your knees.” Negan had instructed, swinging Lucille in a threatening manner.

You dropped instantly to the ground; your knees sinking into the sodden earth beneath you. You glanced toward your companions; you’d scarcely known them a week when The Saviors came looking for the group.

Chancing a look at your captors your gaze fell upon Simon standing tall and threatening before you. His eyes caught yours and there was something in the way he looked at you, which made you feel as though there was hope for your situation.

“Negan,” Simon broke eye contact long enough to address the man in charge. “I’d like, to request the girl… Come back with us to The Sanctuary.” His eyes locked with yours again; a smirk on his lips.

A combination of relief and dread consumed you at Simon’s request, because at least this meant you wouldn’t meet a bloody end by means of Lucille, but it also didn’t mean you were safe.

Negan nodded slowly. “You know I hate killing women,” He ran a gloved hand over his bristled chin and smiled. “Especially one as pretty as _you_ , doll.”

\---

“You know I love you?” Simon whispers, holding you close to him.

“I know.” You smile.

“I’ll always love you.”

“I love you, too.”

And the way Simon looks at you now still makes you feel as though there is hope for your situation; because somehow, in this post-apocalyptic, nightmare world you find yourself in, you’ve got something – someone – worth living for.

**Notes for the Chapter:**

> Look this one was FUCKING DIFFICULT okay I hope it's not horrific but I could only do what I could do with the first line and I didn't want to go for the obvious so... Thoughts?  
> Anywhooo thanks for reading all of these! Originally there were 12 prompts that were set (by my group on twitter) but there is a 13th, bonus prompt. I'll get to that when I can.  
> I'm out of words right now.
> 
> I'm also still considering requests for Simon/Reader so if you have any, throw them my way in a comment and I'll see what I can do. XO


	13. If You're Bored, Wanna Have Sex?

“If you’re bored, wanna have sex?” His voice causes you to jump and you sit up in the passenger seat. Turning your head to the right, you find Simon leaning against the truck door with his arms folded across the rolled down window; a suggestive grin plastered across his face.

“I’m not bored, I’m just...” You want to tell him you’re trying to catch up on sleep, but you know he’ll only smirk knowing it’s _his_ fault entirely you’ve not been getting enough.

He reaches his arm through the window and trails his hand along the inside of your thigh, before pressing his fingers firmly between your legs. And the thought of his fingers sinking into you is enough to make your breath hitch and your hips rock ever-so-slightly forward.

“Gary’s gonna be a while fixing the truck,” Simon states. You glance at the stationary convoy ahead. One of the trucks had broken down and –

_Oh, fuck, Simon_.

You shove his hand away, glaring at him. He smirks and stares back; you know _he knows_ you don’t really want him to stop.

You hesitate a moment as he pulls the door open, raising an eyebrow and nodding for you to exit the truck. You sigh, defeated.

“ _Shit..._ ” You mutter with a grin. “Okay, you win.”

Simon takes your hand, leading you across the grass verge toward the trees.

“ _Hey, Gary!_ ” He calls. “ _How long you gonna be?_ ”

“ _Half hour?_ ” He calls back.

Simon glances at you. “Long enough.” He grins.

**Notes for the Chapter:**

> Okay. I'm done with these prompts. But never fear I already have another list of 13 prompts to work through SO EXPECT MORE SIMON.  
> I appreciate all the love and support and comments and kudos. Ya'll are awesome.


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